On Friday, July 31, 1964, Reeves and his business partner and manager Dean Manuel (also the pianist of Reeves's backing group, the Blue Boys) left Batesville, Arkansas, en route to Nashville in a single-engine Beechcraft Debonair aircraft, with Reeves at the controls. The two had secured a deal on some real estate (Reeves had also unsuccessfully tried to buy property from the LaGrone family in Deadwood, Texas, north of his birthplace of Galloway).

While flying over Brentwood, Tennessee, they encountered a violent thunderstorm. A subsequent investigation showed that the small airplane had become caught in the storm and Reeves suffered spatial disorientation. The singer's widow, Mary Reeves (1929–1999), probably unwittingly started the rumor that he was flying the airplane upside down and assumed he was increasing altitude to clear the storm. However, according to Larry Jordan, author of the 2011 biography, Jim Reeves: His Untold Story, this scenario is refuted by eyewitnesses known to crash investigators who saw the plane overhead immediately before the mishap, and confirmed that Reeves was not upside down. Fellow friend and legendary musician Marty Robbins, recalled hearing the wreck happen and alerting authorities to which direction he heard the impact. Jordan writes extensively about forensic evidence (including from the long-elusive tower tape and accident report), which suggests that instead of making a right turn to avoid the storm (as he had been advised by the approach controller to do), Reeves turned left in an attempt to follow Franklin Road to the airport. In so doing, he flew further into the rain. While preoccupied with trying to re-establish his ground references, Reeves let his airspeed get too low and stalled the aircraft. Relying on his instincts more than his training, evidence suggests he applied full power and pulled back on the yoke before leveling his wings—a fatal, but not uncommon, mistake that induced a stall/spin from which he was too low to recover. Jordan writes that according to the tower tape, Reeves ran into the heavy rain at 4:51 p.m. and crashed only a minute later, at 4:52 p.m.

When the wreckage was found some 42 hours later, it was discovered the airplane's engine and nose were buried in the ground due to the impact of the crash. The crash site was in a wooded area north-northeast of Brentwood approximately at the junction of Baxter Lane and Franklin Pike Circle, just east of Interstate 65, and southwest of Nashville International Airport where Reeves planned to land.

On the morning of August 2, 1964, after an intense search by several parties (which included several personal friends of Reeves including Ernest Tubb and Marty Robbins) the bodies of the singer and Dean Manuel were found in the wreckage of the aircraft and, at 1:00 p.m. local time, radio stations across the United States began to announce Reeves's death formally. Thousands of people traveled to pay their last respects at his funeral two days later. The coffin, draped in flowers from fans, was driven through the streets of Nashville and then to Reeves's final resting place near Carthage, Texas.